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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-19 21:22:52 UTC
HMDB IDHMDB0000961
Secondary Accession Numbers
  • HMDB0004201
  • HMDB00961
  • HMDB04201
Metabolite Identification
Common NameFarnesyl pyrophosphate
DescriptionFarnesyl diphosphate, also known as farnesyl-pp, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesyl diphosphate is considered to be a practically insoluble (in water) and relatively neutral molecule. Farnesyl diphosphate has been found in human testicle tissue, and has also been primarily detected in blood. Farnesyl diphosphate can be found anywhere throughout the human cell, such as in mitochondria, cytoplasm, endoplasmic reticulum, and peroxisome. Farnesyl diphosphate exists in all eukaryotes, ranging from yeast to humans. In humans, farnesyl diphosphate is involved in the rosuvastatin action pathway, the atorvastatin action pathway, the ibandronate action pathway, and the lovastatin action pathway. Farnesyl diphosphate is also involved in several metabolic disorders, some of which include lysosomal acid lipase deficiency (wolman disease), the cholesteryl ester storage disease pathway, the acute intermittent porphyria pathway, and the mevalonic aciduria pathway. Outside of the human body, farnesyl diphosphate can be found in a number of food items such as canola, garden onion, cornmint, and bog bilberry. This makes farnesyl diphosphate a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
(2E,6E)-Farnesol diphosphateChEBI
(2E,6E)-Farnesyl diphosphateChEBI
(2E,6E)-Farnesyl pyrophosphateChEBI
(all-e)-Farnesyl diphosphateChEBI
(e,e)-Farnesyl pyrophosphateChEBI
2-trans,6-trans-Farnesyl pyrophosphateChEBI
all-trans-Farnesyl pyrophosphateChEBI
Farnesyl diphosphateChEBI
trans,trans-Farnesyl diphosphateChEBI
trans-trans-Farnesyl diphosphateChEBI
(2E,6E)-Farnesol diphosphoric acidGenerator
Farnesyl pyrophosphoric acidGenerator
(2E,6E)-Farnesyl diphosphoric acidGenerator
(2E,6E)-Farnesyl pyrophosphoric acidGenerator
(all-e)-Farnesyl diphosphoric acidGenerator
(e,e)-Farnesyl pyrophosphoric acidGenerator
2-trans,6-trans-Farnesyl pyrophosphoric acidGenerator
all-trans-Farnesyl pyrophosphoric acidGenerator
Farnesyl diphosphoric acidGenerator
trans,trans-Farnesyl diphosphoric acidGenerator
trans-trans-Farnesyl diphosphoric acidGenerator
(e,e)-Farnesyl diphosphateHMDB
2-trans,6-trans-Farnesyl diphosphateHMDB
Farnesyl-PPHMDB
trans-Farnesyl pyrophosphateHMDB
trans-trans-Farnesyl pyrophosphateHMDB
Farnesyl pyrophosphate, (e,e)-isomerMeSH
Farnesyl pyrophosphate, (e,Z)-isomerMeSH
Farnesyl pyrophosphate, (Z,e)-isomerMeSH
Farnesyl pyrophosphate, (Z,Z)-isomerMeSH
FarnesylpyrophosphateMeSH
Chemical FormulaC15H28O7P2
Average Molecular Weight382.33
Monoisotopic Molecular Weight382.131027238
IUPAC Name{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Name[hydroxy([(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy)phosphoryl]oxyphosphonic acid
CAS Registry Number13058-04-3
SMILES
[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
InChI KeyVWFJDQUYCIWHTN-YFVJMOTDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP2.4ALOGPS
logP3.62ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity96.73 m³·mol⁻¹ChemAxon
Polarizability37.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-7943000000-ab6d749700f510a94133View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-1469000000-e3fd27c0418d0977f84eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6791000000-1ca128d2b96287a5b2f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q29-9820000000-3277fbdf16e288ab1142View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0409000000-f8bbf786ee9d33cb48d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9501000000-8d060d3ceac94de45b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a265a369e6802359a7dfView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Biospecimen Locations
  • Blood
Tissue Locations
  • Neuron
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0086 (0.0000-0.0170) uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07780
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022339
KNApSAcK IDC00007268
Chemspider ID393270
KEGG Compound IDC00448
BioCyc IDFARNESYL-PP
BiGG ID35006
Wikipedia LinkFarnesyl pyrophosphate
METLIN ID403
PubChem Compound445713
PDB IDFPP
ChEBI ID17407
References
Synthesis ReferenceCastillo-Bocanegra, Rafael. Synthesis and biological activity of farnesyl pyrophosphate analogs. University of California, San Francisco., 1977 - Farnesol  p.364
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Notarnicola M, Messa C, Cavallini A, Bifulco M, Tecce MF, Eletto D, Di Leo A, Montemurro S, Laezza C, Caruso MG: Higher farnesyl diphosphate synthase activity in human colorectal cancer inhibition of cellular apoptosis. Oncology. 2004;67(5-6):351-8. [PubMed:15713990 ]
  2. Shellman YG, Ribble D, Miller L, Gendall J, Vanbuskirk K, Kelly D, Norris DA, Dellavalle RP: Lovastatin-induced apoptosis in human melanoma cell lines. Melanoma Res. 2005 Apr;15(2):83-9. [PubMed:15846140 ]
  3. Argmann CA, Edwards JY, Sawyez CG, O'Neil CH, Hegele RA, Pickering JG, Huff MW: Regulation of macrophage cholesterol efflux through hydroxymethylglutaryl-CoA reductase inhibition: a role for RhoA in ABCA1-mediated cholesterol efflux. J Biol Chem. 2005 Jun 10;280(23):22212-21. Epub 2005 Apr 6. [PubMed:15817453 ]
  4. Reigard SA, Zahn TJ, Haworth KB, Hicks KA, Fierke CA, Gibbs RA: Interplay of isoprenoid and peptide substrate specificity in protein farnesyltransferase. Biochemistry. 2005 Aug 23;44(33):11214-23. [PubMed:16101305 ]
  5. Tacer KF, Haugen TB, Baltsen M, Debeljak N, Rozman D: Tissue-specific transcriptional regulation of the cholesterol biosynthetic pathway leads to accumulation of testis meiosis-activating sterol (T-MAS). J Lipid Res. 2002 Jan;43(1):82-9. [PubMed:11792726 ]
  6. Saisho Y, Morimoto A, Umeda T: Determination of farnesyl pyrophosphate in dog and human plasma by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1997 Oct 1;252(1):89-95. [PubMed:9324945 ]
  7. Sanders JM, Song Y, Chan JM, Zhang Y, Jennings S, Kosztowski T, Odeh S, Flessner R, Schwerdtfeger C, Kotsikorou E, Meints GA, Gomez AO, Gonzalez-Pacanowska D, Raker AM, Wang H, van Beek ER, Papapoulos SE, Morita CT, Oldfield E: Pyridinium-1-yl bisphosphonates are potent inhibitors of farnesyl diphosphate synthase and bone resorption. J Med Chem. 2005 Apr 21;48(8):2957-63. [PubMed:15828834 ]
  8. Fukuchi J, Song C, Ko AL, Liao S: Transcriptional regulation of farnesyl pyrophosphate synthase by liver X receptors. Steroids. 2003 Sep;68(7-8):685-91. [PubMed:12957674 ]

Enzymes

General function:
Involved in transferase activity
Specific function:
Not Available
Gene Name:
FDFT1
Uniprot ID:
P37268
Molecular weight:
48114.87
Reactions
Farnesyl pyrophosphate + NAD(P)H → Squalene + Pyrophosphate + NAD(P)(+)details
Farnesyl pyrophosphate → Pyrophosphate + Presqualene diphosphatedetails
Farnesyl pyrophosphate + NADPH + Hydrogen Ion → Squalene + Pyrophosphate + NADPdetails
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name:
GGPS1
Uniprot ID:
O95749
Molecular weight:
34870.625
Reactions
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphatedetails
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + Geranylgeranyl-PPdetails
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:
FDPS
Uniprot ID:
P14324
Molecular weight:
48275.03
Reactions
Geranyl-PP + Isopentenyl pyrophosphate → Pyrophosphate + Farnesyl pyrophosphatedetails
General function:
Involved in protoheme IX farnesyltransferase activity
Specific function:
Converts protoheme IX and farnesyl diphosphate to heme O (By similarity).
Gene Name:
COX10
Uniprot ID:
Q12887
Molecular weight:
Not Available
Reactions
Heme + Water + Farnesyl pyrophosphate → Heme O + Pyrophosphatedetails
General function:
Involved in protein prenyltransferase activity
Specific function:
Catalyzes the transfer of a farnesyl or geranyl-geranyl moiety from farnesyl or geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. The alpha subunit is thought to participate in a stable complex with the substrate. The beta subunit binds the peptide substrate. Through RAC1 prenylation and activation may positively regulate neuromuscular junction development downstream of MUSK (By similarity).
Gene Name:
FNTA
Uniprot ID:
P49354
Molecular weight:
44408.32
Reactions
Farnesyl pyrophosphate + protein-cysteine → S-farnesyl protein + Pyrophosphatedetails
Farnesyl pyrophosphate + Protein-cysteine → S-Farnesyl protein + Pyrophosphatedetails
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Catalyzes cis-prenyl chain elongation to produce the polyprenyl backbone of dolichol, a glycosyl carrier-lipid required for the biosynthesis of several classes of glycoprotein.
Gene Name:
DHDDS
Uniprot ID:
Q86SQ9
Molecular weight:
Not Available
Reactions
Farnesyl pyrophosphate + → Dehydrodolichol diphosphate + details
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a farnesyl moiety from farnesyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins. The beta subunit is responsible for peptide-binding.
Gene Name:
FNTB
Uniprot ID:
P49356
Molecular weight:
48773.2
Reactions
Farnesyl pyrophosphate + protein-cysteine → S-farnesyl protein + Pyrophosphatedetails
Farnesyl pyrophosphate + Protein-cysteine → S-Farnesyl protein + Pyrophosphatedetails
General function:
Not Available
Specific function:
Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:
PDSS2
Uniprot ID:
Q86YH6
Molecular weight:
44128.17
Reactions
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + all-trans-Decaprenyl diphosphatedetails
General function:
Not Available
Specific function:
Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:
PDSS1
Uniprot ID:
Q5T2R2
Molecular weight:
46260.6
Reactions
Farnesyl pyrophosphate + Isopentenyl pyrophosphate → Pyrophosphate + all-trans-Decaprenyl diphosphatedetails